5 Years of Startups: What I Wish People Had Told Me

Backstory: I’ve been doing startups for the past 5 years. I’ve been in 4 startups, 2 as an employee and 2 I’ve founded. The 2 I’ve founded went through Y Combinator S12 and S14 batch.

[You can check out what I'm currently working on here]

1. Don’t do it for the money unless you’re shooting for billions

I don’t think I’ve ever decided to do a startup just for the money but I’d be lying through my teeth if I told you that money wasn’t a factor. I think because in the states it’s a bit of a taboo to openly ever admit that you’re doing something just for the money that many people lie to themselves about their actual inner ambitions as people may label you as a sellout or someone who has shallow ambitions. On the contrary though, I think it’s perfectly alright to do something just for money as long as you can be honest with yourself.

However, if you’re doing a startup just for the money, the unfortunate truth is that startups are a terrible way to make money. There are plenty of easier ways to make a million dollars than going through the hardships of founding a startup that will statistically likely fail.

Alternative routes such as working a decent paying job and investing it for 20 years will guarantee millions of dollars with higher certainty than 20 years of startups. During those 20 years, you’ll probably end up working a lot less and being more mentally comfortable too. If that doesn’t sound great to you and you’re unwavering in your love for startups and technology, you can always just join an early stage startup or even a mid stage rocket ship of a company and make millions of dollars that way.

The only contradiction is if you’re aiming to make billions of dollars then startups are actually a great path to billions, if not one of the only paths to a billion dollars. But if this is your goal, be honest with yourself and be sure that that’s what you really, really want. Is your pursuit really money? Do you really want to become a billionaire? What would you even do with all of that money?

Again, I don’t think money is a shallow pursuit by any means. I just don’t think it’s a good anchor for motivation while doing a startup because reality doesn’t often times line up with expectation.

Once you find yourself in the deepest darkest hole of your startup and begin doing the mental calculations in your head on whether or not you should quit, you’ll think about how much money you’ve lost, the opportunity cost, how much time and wasted energy, and if money was your only anchor, you’ll probably quit.

2. It’s going to be a lot harder than you think

People always say it’s hard but I never quite personally believed it. When someone tells you something is hard, if you’re the type of person that likes challenges, you’ll likely tell yourself, “Pssh, I’ve been through a lot. It can’t be that bad”.

But it really is likely the hardest thing you’ll ever attempt in your life.

For one, it’s a huge toll on the psyche. It’s like building up your morale and courage and then getting rejected over and over and over again.

As Peter Thiel points out, good startup ideas often look like really bad ideas. If it was a good idea, everyone would have been scrambling to do it. It’s only a good idea in your eyes because you probably have market expertise or a vision that many other people don’t have. For those that are uninformed, you just look crazy to them.

And that’s the problem. You’re going to look crazy. Not only to investors but to colleagues, to acquaintances and new people you meet, and most importantly to your friends and family. A lot of them won’t understand what you’re doing. Some might even think it’s stupid and it’ll be one of the most discouraging things you’ll face.

Can you continue working on your startup when the closest people to you all think you’re wasting your life on something that won’t go anywhere? Can you continue working on your startup when your significant other suggests you should go back working a “regular job” so you guys can have a more stable life?

Startups can and will eat away at your life if you’re not careful. It starts with just one late night, then two, then three then you’re working late night on weekends, now you’re working on vacations, then before you know it you haven’t taken a vacation in two years. It doesn’t always have to be like this but without careful introspection you will lose close friends, you will become more distant with your family. It will creep on you and if you let it, you’ll probably be faced with some of the most impossible choices you’ve ever had to make in your life.

3. It’s going to be a lot more rewarding than you think

On the positive side, as difficult as I’ve found startups to be, not many people have told me how positive and rewarding the experience will be either.

I believe that entrepreneurs are a particular type of people. Not in the sense that one has an engineering background and one with a marketing background, but I think there are very specific traits bring us together.

Entrepreneurs are curious and usually asks a lot questions. They’re akin to that annoying kid that always raises their hand in school. They’re also driven to where they’re always trying to find ways to improve and optimize inefficient systems. They are the type of person that says, “if I had 2 rubber bands a pen, I could probably build a better XYZ than that hunk of junk”.

They’re obsessed to the point where the only things that occupies their minds sometimes is how to solve a particular problem. Sometimes it’s difficult to get in contact with them or communicate with them because they’re off in their own worlds.

They’re rule breakers, ever teetering on the edge of what is legally and morally right. Sometimes it’s scary to be associated with them because you don’t know if you’ll get in trouble as well.

I don’t think entrepreneurs make the best friends. They often times can appear bizarre, eccentric, distant, uncaring, overly opinionated. I feel like if you were entrepreneurial in a sea of people who weren’t, you would easily feel frustrated and crazy.

And I think that’s exactly why if you felt like you had the calling to DO something; to create something and you took the leap of faith despite whatever logic telling you not to, you might find yourself in a place amongst people who also share grandiose delusions as you and the feeling that you belong and why the journey, despite how difficult it may be, might end up being worth it for the experience alone.

That was Y Combinator for me. Throughout school, I’ve always felt frustrated at “the man” for holding me down and with what I felt were to be set paths that I didn’t particularly agree with. When I made the leap into this bizarre world of startups and entrepreneurship, you slowly begin to realize that no one really knows what they’re doing either, we’re all a little bit scared, and on the inside, all might be a bit a little crazy as well. For me, this has been the amazing experience of feeling like I’m not alone.

Mistakes I’ve made as a technical founder

(As always, you can check out what I’m currently working on here)

#1 The “one more feature / bug fix” mentality

Sometimes when my product isn’t launched yet, I ask myself why. I kick back and say to myself that the product isn’t ready, it has too many bugs, or that it doesn’t have this one core feature. That’s how I know I’m probably in the “one more feature” denial state. As technical people, I think we have a tendency to want things to be as perfect as possible and end up delaying for as long as possible.

Selling things can be scary and having people use your products that you know is broken is even scarier. We’re builders and building things is fun and safe, so we often times I find ways to really convince myself that all it takes is just “one more feature”.

#2 We’re quick to think that our problems are rooted in a technical flaw rather than non-technical one

Everyone has a bias and when trying to tackle a problem, rather than thinking from first principles we often draw from heuristics. Since my past experiences have been predominantly technical, I naturally have a tendency to want to solve my issues in a technical way.

“Why aren’t we growing fast enough?”
– “Well, we don’t have features x y and z” rather than “We aren’t marketing it well enough”

“Why are people leaving our site?”
– “It’s buggy and hard to use” rather than “The experience is lackluster and is confusing to use”

“Why do people use our competitor rather than us?”
– “They’re well funded and offer these features where we don’t have!” rather than “We just suck at selling”

This leads back to point #1 where I might just keep on recursively building and building and building.

#2.1 Build it and they will come

This sort of relates to points #1 and #2. As a technical person, I’ll admit that I’ve neglected and failed to acknowledge the importance of sales and marketing early in my career. Because of my “one more feature” mindset, I get into the mental state that somehow, once this feature is done and the product is perfect, we’ll launch it and everything will be fantastic and everyone will want to use it.

Obviously, this has never worked out for me.

#3 We’re quick to pitch features rather than solutions

Technical founders with no previous sales experience often make pretty poor sales people. It makes sense because as a builder, sometimes I can be more focused on the micro rather than the macro. I’ll talk about things that personally excite me and don’t realize when other people just don’t care.

I’m sure we’ve all been there before. You spent a week working on this feature and you’re super proud of it. UI / UX wise, it might not be the most impressive thing to show, but holy crap, look at how fast it is!

I think often times, it becomes a huge problem when technical founders take this mindset into selling their product. They sell the components and features of the product rather than the solution: “Look at how pointy this spear is!! It’s proven to be 2x more sharp than a regular spear! The stick of the spear is made from a special wood that makes it so you’re a lot less likely to get splinters!”

Rather than, “When Mongolians are barging into your front door, this spear will offer you the best chance at saving your life”.

You have to know what problems your users has and pitch directly to that solution. I’ll write a blog post on selling as a technical founder later. 

#4 We have lower pain tolerance and quick to beat ourselves up

One thing I realized about myself before I started getting more into sales is that I have a lower pain tolerance than my sales person counterparts. Whereas sales people will often hear “No” or even “No, this product sucks” several times a day, if we’re technical, particularly if we’re sheltered, we might only get to hear it once every couple weeks or once a month. When we DO hear it, it feels terrible. We start questioning our competency, we beat ourselves up, and its a huge hit on our morale.

Part of the lesson on becoming a good sales person is having a short term memory and realizing that negatives comments about the product does not reflect on your competency.


My personal struggles with learning how to program

(As always, you can check out what I’m currently working on here)

5 years ago I was in my third year of biology hoping to get into medical school. I didn’t know much at all about programming besides what I had learned by making custom maps in Starcraft and Warcraft, but I had decided to enroll in a basic programming class as part of a graduation requirement.

I remember it was a huge challenge at first. The first program I wrote, a basic “Hello World” wouldn’t compile and I couldn’t figure out why. When I went to ask a friend for help, he pointed out that I had simply missed a semi-colon. A semi-colon. It seems a bit silly to think back to that then, but that was really how I started. Square one.

I remember my other colleagues seemed to blaze past me in the class as it felt like they were all taught how to program by their parents at the age of 5 who all worked at Microsoft (I went to the University of Washington). How was I supposed to catch up with that?

It was very discouraging and I know it sounds a bit silly, but at the age of 19 I felt TOO old. I felt so stupid. I was dejected and I remember giving up on programming time and time again whenever I found myself stuck. I felt like I had such grand ideas in my head, but didn’t know how to communicate them with my limited knowledge of the language and whenever I went to ask someone for help, they’d always suggest me to scale back my ideas like, “oh, have you tried just doing this basic thing in JavaScript instead?” It’s one of the most frustrating feelings as it feels like you’re just screaming in your head without being able to communicate sometimes.

I made a lot of excuses to quit such as “eh, I don’t really need this that much for my career anyways.”.. “If I really wanted to learn programming, I should have done it years ago”… “I’m more into the natural sciences, I don’t think I’m really well suited for this”. I made a lot excuses and I “quit” many, many times. I guess eventually I just quit and failed so many times that eventually I just became a decent programmer and entrepreneur?

Anyways, I don’t know exactly where I’m going with this but I just wanted to share my story with you all since I know I’m probably not alone in this boat. If you’re learning how to program and you’re frustrated, it’s normal and you’re probably doing it right. Some people learn at a younger age, some people come from a completely different background like me and struggle a bit more than others. Learning how to program was and still is a really long journey and you won’t regret it so keep at it!

If you ever needed any advice or had any questions, feel free to shoot me an email at vu0tran@gmail.com.

5 Reasons Being a Solo Founder Sucks

I’ve recently began the journey of doing another startup. If you haven’t seen it, you can get a sneak preview here. The difference this time around is that I’m doing it solo.

They say writing can help keep you mentally fit, so why not: my five takeaways of being a solo founder. (I’ll follow this up later with five things I enjoy about being a solo founder)

Serious lack of high fives

The early days can be one of the most difficult times for a startup. You’re still trying to build your product, you’re still trying to validate it in the market and when you lose moral, a lot of times its game over.

It’s also the time where you probably won’t have any employees yet and as a solo founder, you’re going to be completely alone. I recall some of my biggest early victories in the only short time span I’ve done this current start up. In the past, I had other co-founders with me that I could celebrate with, that I could feel excited and victorious with.

When you’re a solo founder, sometimes it can feel like you’re just popping a champagne bottle alone.

When you’re not smiling, no one else is smiling

I heard someone say that as a team of two co-founders, as long as one person is smiling and in good spirits at any given time, the startup will be okay. As a solo founder, you’re probably going to be your biggest pillar to lean on so if you don’t have the ability to motivate and pick yourself up, you won’t last very long going solo.

Startups only die when founders quit so when you lose your moral and can’t pick yourself up, your startup will die.

You have to task switch a lot

Having to do a lot of things at once means that you’ll probably be more stressed while doing everything at a lower quality. The efficiency in having co-founders is that your team can very early on fall into specializations.

There’s a lot of mental overhead in having to be able to watch over the product, talk to users, design and build the product all simultaneously. Your mental cache is only so big and every time we switch between tasks, there’s going to be some down time to get revamped up on where we once were.

It’s easy to swerve dangerously

There’s a phenomena where if you were to drop anyone in a large field in near pitch blackness and tell them to walk straight, they’ll almost always literally walk in circles.

The thing is, without any visual reference point, it’s hard to know initiatively where we’re going.

One way to counteract this, I hear, is by walking with a partner. Two people walking shoulder to shoulder will help correct our natural tendency to want to swerve and go around in circles.

Hey, I know it’s a far fetched analogy, but I think there’s a lot of parallels in that and in running a startup as well. Unless you’re a very introspective person, it’s very easy to get tunnel vision in what you’re doing. A co-founder is someone you can trust to help you make those corrections when you start swerving.

It’s distracting to be alone

Being alone sucks and arguably even for the deepest of introverts. I think its in human nature to eventually want some sort of human contact and a lot of times when co-founding a company, your other co-founder is sufficient.

Without that, you’ll probably find yourself needing to hang out with friends, find other people to help motivate you, join meetups, networking events, conferences, etc. All of that is less time you can be working on your product.

My smart phone has made me dumber

Has anyone ever noticed how smart phones have actually made us dumber? Before smart phones, whenever I had spare time waiting for something, whether its the bus or the dentist, that’d be my chance to think and reflect. There was just nothing else to do.

Now all I do is bring up Facebook, Reddit or email. I end up thinking less.

Before when I might be out with a group of friends and we didn’t know the answer to something, we’d try to apply our knowledge with logic to figure it out. We worked our brains.

Now all I do is pull up my phone and look it up. The answers are easy.

A big part of making yourself smarter is being able to reflect and critique yourself. I certainly have done it less since I’ve had my smart phone. I remember times where I might have gone to bed too early. I wasn’t tired enough to sleep, but I wasn’t awake enough to get up and go back to my desktop computer to browse the web. I just laid in bed and thought. Now I just browse my phone.

I’ve used my brain less. I’ve had less opportunities to think through hard problems and I think I’ve probably become dumber because of it.

The next time you’re bored and find yourself reaching for your phone, try to keep it in your pocket and let me know where it takes you.

3 Years Since Rejection

Wow! I can’t believe it has only been 3 years since I got rejected from the University of Washington CS program.

It feels like I’ve lived 10 years since then with all the crazy things I’ve been fortunate enough to experience.

I still remember how angsty, disappointed and disheartened I was at the time. I remember telling someone that if I didn’t get in, I wouldn’t know what to do with my life. It was the only thing I had planned for myself and it was the first time in my life where I felt like I didn’t know what to do.

Regardless, after the rejection, I felt like the only thing I could do was to pick myself up and find an internship. I applied to 15+ companies, and got rejected from all of them. Amazon, Microsoft, Facebook, F5, Zillow, Google (twice) along with other medium sized companies. Talk about rubbing salt on an open wound. I went from feeling disheartened to feeling absolutely curb stomped.

I nearly gave up, but kept on reminding myself of the statistics. If I applied to 1000 places, surely, I would get a job at one? It wasn’t until I applied to work at a startup as the first employee that I was accepted. I remember the interview with the CEO. He never even bothered to ask me any technical coding questions at all. He gave me the job on the spot and when I asked why, he just told me, “I don’t know, I just saw something in you.”

This set in motion a series of strange events – from intern to a director, from writing scrapers in Java to authoring specs that almost all of you guys interact with on a daily basis. From working for others, to being part of YC to help found our own company and fundraise.

Everyone wears a mask and sometimes you just don’t see how hard others have to struggle. We are all main characters in our own movies.

It’s funny looking back because the amount of catastrophic failures I’ve experienced haven’t stopped. In fact, they’ve only increased in frequency and now in greater magnitude. I fail so much harder now.

From back then to now, I think the only thing that has changed is my attitude. Failing is just life’s way of telling you that you were meant to achieve bigger things. Because success is a mirage and never looks like what it appears to be. It’s generally a string of progressively getting better at failing. If you set yourself up to where you can see yourself fail, only then can set yourself up for success. Do or do not. There is no try.

It’s amazing to think that what felt to me like my worst failure at the time was the best thing that ever happened to me. It’s great because I almost get monthly emails from recruiters from companies such as, Amazon, Microsoft, Facebook, and this time around, I’m the one dishing out the rejection.

Here’s to our next 100 failures! 

Make something people want (to pay for)

YC is famous for its mantra, “Make something people want”. It’s short, sweet and it makes sense… until you start thinking about it.

“But how do I know people actually WANT this?”

I think you can generally figure this out by asking people one thing, “how much would you be willing to pay for it?”

The failure to identify whether someone actually wants your product vs someone being largely apathetic is difficult to distinguish. Mostly because the people you might initially be talking to are your friends and family. These people don’t want to let you down. They’ll also already be excited because they will be excited for you. It’s hard to cut the crap.

Let’s imagine you’re building a social network for dogs and you’re pitching to one of your friends who’s a huge dog lover.

You: Yeah, this website is going to be great! You can upload pictures of your dog, communicate with a million other dog lovers, share stories! It’ll be amazing!

Your friend: Wow! That’s an awesome idea! I would love to use something like this!

With this conversation, you haven’t validated your product in any way. Any seasoned sales person knows that all this really shows is that there’s interests in your product, not exactly validation that they really want it. I know because as a developer trying to improve on my hustling, I personally make this mistake a lot. ( I still do).

I think to myself, “Great! This person is within my target demographic and she says she really wants the product! This means there’s validation!”


All they’re essentially saying is that if this product as you have described to them were to exist today, they would consider using it but thats it.

Okay, so how should you follow up with this conversation then?

You: Yeah, this website is going to be great! You can upload pictures of your dog, communicate with a million other dog lovers, share stories! It’ll be amazing!

Your friend: Wow! That’s an awesome idea! I would love to use something like this!

You: Awesome! How much would you be willing to pay for it?

Your friend: Hmm, I don’t know. I’m not sure if it’s a product I’d exactly pay for.

If that’s their response, then you can almost guarantee that they don’t really want your product. If they’re not willing to pay for something, then it probably means you haven’t yet identified a product that serves any of their current need. In other words, they don’t want it.

However, this doesn’t exactly mean that your product sucks. It could just be that you’re pitching it wrong or that your idea needs some tweaking. Take for instance, a different approach:

You: Yeah, I’m building a website that enables you to book pet sitters for your pets!

Your friend: Wow! That’s an awesome idea! I would love to use something like this!

You: Awesome! How much would you be willing to pay for it?

I know it’s just an imaginary exercise, but I’d argue that even without knowing what your friend is going to say, intuitively, this approach has a better chance of her telling you that she might pay for it. The pitch was specific and identified a need.

Perhaps she’s been looking for a sitter for a while but can’t find a good one and would be willing to pay $5 for it. Who knows, but at least what this demonstrates that with this method of thinking, rather than building something that’s just cool, you’ve began to think of something that is actually catered to a specific problem someone out there is having.

The point is, if you’re working on a project where you can’t imagine trying to ask someone to pay for your product, then you’re probably not building anything people want.

It doesn’t matter if you’re even charging for your product or giving away for free on the App Store. I think even if you intended on giving away your product for free, you should always be in the mindset to make a product that’s so good that people would want to pay for it anyways.

Does fear of failure drive success?

In one of Paul Graham’s essays, “How Not To Die“, he simply states:

“So if you want to get millions of dollars, put yourself in a position where failure will be public and humiliating.”

Awesome, so if I want to succeed and get a million dollars, all I have to do is be afraid of failing, right? Well, I don’t exactly agree so much with Paul Graham on this one, and here’s why.

I don’t think fear of failure drives success as much as I think that fear of failure is a byproduct of putting yourself in a position where you CAN achieve success.

A little bit of background on myself. I work in the tech industry and startups are all I’ve known. So far, I’ve worked for 3 startups and did a YC company.

Right now, I’m a Dogecoin advocate and  I consider Dogecoins to be a lot like a startup in the sense that it can make me feel very similar. When I check the news, when I look at the charts, sometimes I feel the highest of highs but at other times, I can also feel the lowest of lows. It’s a lot like when doing a startup and checking your numbers, “Am I going to hit this week’s quota? Where will we be in 3 months? Is Dogecoin really the right choice? Is our product really the right thing we should be focusing on? Are we the right team to do it?”, etc.

You see, I think what I’ve discovered is that the reason why I was scared and worried is because my path to failure was clearly laid out. I could see it. I could grasp it. It was scary.

If I didn’t hit my targets, we’d be failing. If we couldn’t get x more signups, we’d be failing. If we couldn’t raise x dollars, we’d be failing.

You see, success at all times is binary. If your goal is 10%+ in revenue by the end of the month and you don’t hit it, you didn’t succeed. You failed. There is no in between.

I think the companies that are the most successful can often be the companies that are most afraid to fail because clarity of failure also means clarity of success. Because when we align ourselves to see downwards into the hole of failure, we can also look upward and see the rocket path to success. The companies that are most successful knows what it takes to succeed. They put themselves in the position where they can succeed and where they can also fail.

If we always allow ourselves to be the position where we’re COMFORTABLE, then we will never have RISK and without risk we will remain stagnant. Stagnation is not bad but just know that if we can NEVER FAIL, we can also NEVER SUCCEED.

Blahblah blah, blah blay godoastartup.

Stereotypes of a Seattleite from a Seattleite

  • If you’re a software engineer in your 40s+, you’re going to be wearing khakis in the summer, sandals with socks and a safari hat.
  • You can tell how long someone has been in Seattle by their unwillingness to use an umbrella. “Nah man, it’s just sprinkling.”
  • You can also tell a true Seattleite by the level of disgust in their face when they have to put up with another damn, unoriginal rain joke.
  • We can drive in the rain, but give us 2 inches of snow and the entire city shuts down
  • 90 degrees is too hot.
  • We always thank our bus drivers.
  • Most of us can passionately tell you their favorite place to get their Asian food fix (pho, sushi, thai food, etc.)
  • 50% of you reading this are either driving a Subaru or a Hybrid
  • We’re the most patient  and polite drivers in the world to the point of breaking laws. Even if you don’t have the right of way, some drivers will still block up traffic to let you turn out.
  • The only times a Seattleite experiences anger is when someone cuts down a tree or pollutes a stream. Oh, and against the San Francisco 49ers.
  • Some of our sports teams suck (I’m looking at you, Mariners) but we love them anyways.
  • We’re really proud of our Nirvana and Hendrix.
  • True Seattleites never go to Starbucks but that hipster coffee shop down the street. The barista there is probably tatted up with gauged ears.
  • If you’re between the ages 15-30, you own a plaid / flannel shirt.
  • We know that Seattle is the best city in the world. But we’re just too humble to brag.
  • We love our gays.
  • Recycling is our religion.
  • We love our trees and parks.

The $6,000,000,000,000 Price Tag of War

money falling

It’s estimated that the costs of the Iraq and Afghanistan wars could total around $4 – $6 trillion dollars in a new study released by a Harvard Research.

$6 trillion dollars. When you read that number out loud the shear size of it completely skips over you. The number is so tremendous, that we have nothing to actually compare it to.

How much is $6,000,000,000,000 really?





  • The entirety of the US Interstate System is estimated to have costs $425 billion in 2006 dollars making it the “largest public works program since the Pyramids”. We could have rebuilt the highway system 14 times over. Think of all the new gas pipelines, internet infrastructure, electric cabling, clean energy plants we could have produced.



  • It’s estimated that the first manned mission to the Moon, Apollo 11, costs about $2.2 billion in 2013 dollars. We could have gone to the moon and back 2700 times and still have money left over.
  • $6 trillion is 375 times the current NASA budget.

free money


  • There are 243 million working aged adults in the United States. If we were to divide $6 trillion, each working aged adult would receive $25,000.
  • If the government were to provide you with $5,000 a day or close to $2 million a year for doing nothing for the rest of your life, they’d still be paying you after over a billion days.

Why does it cost so much?

I’ll just leave you with a single example: the $1 trillion plane that doesn’t fly quite right.

The US Government has been pursuing the now infamous joint US Stealth Fighter project for over a decade. At a 1 TRILLION DOLLAR price point, that alone is 1/6th the cost of the wars in the Middle East. $1,000,000,000,000 for just a single stealth fighter program? That’s enough to fund ANOTHER war or if we wanted to put it to actual good use, we’d be able to completely redo the USA’s road, internet, electrical, infrastructure over the next 5 years. It’s no wonder why war prices are so exuberant and is a slippery slope that has long spiraled out of control.

What a waste.